Holiday rentals with a pool in Pensacola

5 out of 5 average rating, 175 reviews

A private pool area is surrounded by a wooden fence, featuring clear blue water and colorful floats. A shaded seating area with vibrant umbrellas and lounge chairs is visible nearby, offering options for relaxation. The atmosphere is bright and inviting, with a glimpse of the bungalow in the background.

Guesthouse in East Hill

Funky Flamingo~ Guest House~ Pool & Kitchenette

This charming East Hill pool bungalow is owner managed/cleaned. Steps from Publix, 1 mile to downtown/Bayfront and just 12 minutes to Beach! Enjoy the private pool & entire back yard. Luxury comforts and amenities, with the highest speed Wi-Fi/streaming services. Casper mattress and pillows with (700 thread count Egyptian Cotton sheets), for an amazing nights rest. Beach chairs, cooler, umbrella and towels provided. Enjoy the new walk-in shower w/ tankless hot water heater. LBGTQIA2S+ friendly!

Home in Downtown Pensacola

A two-story home features a light blue exterior and a symmetrical design, framed by white columns on the porch. The landscaped front yard is neatly manicured, with low shrubbery and a brick pathway leading to the front door.

4.91 out of 5 average rating, 216 reviews

Historic Downtown Bayfront Home Pool Mins to Beach

The Bayfront Manor brings the best of both worlds to your vacation or business stay in Pensacola. Located 5 min walk from historic downtown, Seville Square, and Palafox Street, the location is ideal for all dining, nightlife, and events. The home is positioned on the corner of Bayfront Dr allowing for great water views of Pensacola Bay. The best beaches on the Gulf are only a 10 min drive. The location is also great for wedding parties as the Barkley House and Christ Church are walkable.

The living area features a comfortable gray sofa set, a white coffee table, and a ceiling fan. Natural light enters through sliding glass doors leading to a private patio. An open kitchen with wooden cabinetry and a dining area is visible, highlighted by bar stools at the counter.

4.97 out of 5 average rating, 205 reviews

$0 clean fee! Beachside/pool view/king bed/jacuzzi

Perfect little place for couples or small families to get some R&R. This condo has a poolside view in a lovely little complex, and is just one building back from the beach - steps from paradise! The Gulf boasts some of the most beautiful beaches in the world, and this is the perfect location tucked away from the busy crowds but still close to restaurants, activities, live music, national parks, and a world class spa. The condo is well-equipped and recently updated in October 2022. Come enjoy!

A private balcony offers sweeping views of the Gulf of Mexico, showcasing the clear blue waters and soft sandy beach below. The horizon merges sky and sea, creating a serene coastal scene. Beach chairs and umbrellas are positioned along the shoreline, inviting relaxation.

4.98 out of 5 average rating, 213 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

**Recently Updated Interior!** Experience the stunning Gulf of Mexico from the comfort of this beachfront 2-King bedroom, 2-bath condo located directly on Pensacola Beach! Nothing separates you from the best white-sand beach on the Gulf Coast. This beach condo boasts a vibrant interior filled with beach-themed accents, a private balcony with sweeping ocean views, and access to 2 pools (1 heated) and a hot tub. Enjoy the best restaurants and shopping on the beach, all within a short walk.

4.91 out of 5 average rating, 105 reviews

A living area is displayed, featuring a comfortable gray sofa with decorative yellow pillows. A set of nested coffee tables sits in front, with a simplistic design. A wall-mounted television and a decorative fireplace are visible, while natural light filters through a window adorned with light curtains.

Condo in Pensacola

Stylish 1 bdrm condo. May sleep 4. Just off I10

Enjoy easy access to everything from this perfectly located home base. Totally refurbished. All new appliances and furniture, microwave, dishwasher, washer and dryer, and various utensils. Toiletries initially supplied. Close to shopping malls, restaurants and fast food outlets. Beautiful Pensacola Bch just 20 mins away. Downtown 15 mins NAS 15 mins Airport 10 mins Hospitals 5 mins Check in after 2 p.m. Check out 11 a.m. Pool key provided but must be returned Perfect for work or leisure

5 out of 5 average rating, 123 reviews

Quiet & Cozy Family Home! Perfect Winter Stay!

Welcome to your quiet Pensacola getaway! The perfect home base for beach days, Blue Angels excitement, and relaxing evenings. Located in a peaceful neighborhood just minutes from Pensacola Beach, NAS Pensacola, and downtown, this clean and comfortable home is ideal for families, couples, military visitors, and longer winter stays. Whether you’re here for the sugar-white beaches, aviation events, or a laid-back escape, this home offers space, convenience, and comfort without the crowds.

Guest suite in Gulf Breeze

A private pool area features a crystal clear swimming pool surrounded by lounge chairs and a shaded umbrella. A colorful pool float and games are visible, alongside a seating area with a fire pit, all enclosed in a spacious backyard with green landscaping.

4.93 out of 5 average rating, 157 reviews

Cozy Suite w/ Private Pool near Navarre Beach!

Welcome to Bella Blue! Our beautiful and newly renovated Pool Oasis. Quiet private 2 BR / 1 BA apartment with a private crystal clear pool/ inviting firepit and more. Private fenced spacious backyard for pets. Only 6 Miles from beautiful Navarre beach. Hang out in our family friendly play pool or head to the emerald waters of Navarre beach. Located one mile from the Gulf Breeze Zoo, 15 miles from Pensacola Beach. Conveniently located for shopping /restaurants. We hope you enjoy! Sonya

A bright living area features a comfortable seating arrangement and a wooden dining table for four. Large windows provide views of the beach, allowing natural light to fill the space. A flat-screen TV is mounted on the wall, complemented by beach-themed decor and soft furnishings.

4.93 out of 5 average rating, 184 reviews

Serving Vitamin SEA! Ground floor BEACHFRONT views

Welcome to Perdido Skye!! Our property location is 13785 Perdido Key Dr. Pensacola, FL, 32507. Unit G1. We fell in love with this ground floor, cozy condo with views that connect you to the sugar-white sand beaches and sparkling blue gulf waters. Our corner unit fills the rooms with sunshine and lots of Vitamin SEA and is very accessible to the pool, ocean, grilling area and parking. No hassle or waiting for elevators. HAPPY BEACHING!! Sincerely, Steven and Rebekah

4.97 out of 5 average rating, 174 reviews

The image captures the nighttime view of a screened-in pool area, illuminated by blue lights. The architectural structure showcases a modern design, with clear visibility of the surrounding landscape featuring trees and grassy grounds. Soft lighting enhances the atmosphere, suggesting a serene outdoor space.

Tiny home in Pensacola

Tiny Home Pool View 25 Mins to Beachb

Welcome to our cozy tiny home located in my secured backyard, where a queen-sized bed promises a peaceful night’s sleep and our well-equipped kitchenette simplifies meal preparation. You will have free parking located in the backyard just steps away from the tiny home. Additionally, you’ll have the opportunity to gather around the outdoor fire pit for cozy evenings under the stars. Inside, unwind with a smart TV and stay connected with complimentary Wi-Fi.

A serene view of the bay is captured from the balcony, showcasing the calm water and sandy beach lined with outdoor furniture. In the distance, a pier extends into the water, while boats can be seen sailing peacefully, framed by the clear blue sky.

4.99 out of 5 average rating, 105 reviews

Pensacola Beach Condo w/ Great Views (F12)

Perfectly situated on the quieter west end of Pensacola Beach this 3rd floor walk-up sits on the Pensacola Bay and is a 5 minute walk to the Gulf of Mexico. It’s our first season of hosting guests and we would love to have you. Our condo is less than 1/2 mile to Peg Leg Pete’s - a Pensacola Beach favorite restaurant. If you want a night-out, the Casino Beach and Boardwalk area has more than 10 restaurants and bars and is less than 2 miles away.

An outdoor pool area is enclosed by a screened patio, featuring a rectangular pool and a hammock for relaxation. Comfortable seating is arranged around a coffee table, with greenery adding a touch of nature. A bar with stools is visible, enhancing the outdoor experience.

4.97 out of 5 average rating, 132 reviews

Poolside Retreat, Hot Tub, 5 min to beach

Looking for the perfect place to stay for your beach vacation? Look no further! Our beautiful, newly furnished home has everything you need for the perfect vacation including your own private pool and hot tub!!! The pool is in a screened in enclosure (bye bye bugs) and surrounded by a covered patio with comfy seating, a sit up bar w/beverage fridge, outdoor TV and a dining table for six. Or kick back and relax poolside in our hammock.

A corner of the living area is presented with large windows offering expansive views of the water. A wooden desk and a light-colored chair provide a workspace, while a soft armchair and small table create a cozy seating arrangement. Natural light floods the space.

4.93 out of 5 average rating, 106 reviews

Relax Waterfront, Sunset VIEWS, Secluded Beach

Stunning 2-story unit, fully renovated, with plenty of space to accommodate up to 8 people. • Excellent LOCATION on the quite West end of Pensacola Beach. Last complex before National Park at Ft. Pickens • Gorgeous SUNSET views from both balconies • Just a few steps from the GULF OF MEXICO BEACH – perfect for couples and families! • QUIET AND SECLUDED Beach on Santa Rosa Sound

Popular amenities for Pensacola rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 117 reviews

Poolside Family Retreat w/ Hot Tub & Game Room

A screened-in pool area features a clear, blue pool surrounded by a spacious deck. Lounge chairs are positioned around the pool for relaxation. Lush palm trees and greenery are visible in the background, offering a glimpse of the outdoor environment.

4.93 out of 5 average rating, 110 reviews

Fun, sun, sand, and rest. Enjoy your stay with us.

4.93 out of 5 average rating, 74 reviews

Pickleball Paradise w/Private Hot Tub, Pool & Bar

A serene backyard features a refreshing pool surrounded by lush greenery. Comfortable lounge chairs are positioned under an umbrella, while potted plants add a touch of nature. A patterned outdoor rug connects the seating area to the pool, creating an inviting space for relaxation.

4.87 out of 5 average rating, 94 reviews

Pool House at Indigo Cove, Close to NAS!

An outdoor area features a hot tub alongside a round stock tank pool, each inviting relaxation. A colorful beach ball floats in the stock tank pool. A lounge chair is placed next to the hot tub, surrounded by green grass and gravel.

4.94 out of 5 average rating, 65 reviews

Amazing Hot Tub/ Stock Tank Pool

An adventurous putt-putt golf course is framed by colorful borders in vibrant pink and blue. The course features multiple holes laid out on a lush green surface, surrounded by decorative mulch and plants, with string lights hanging overhead, enhancing the playful atmosphere.

5 out of 5 average rating, 24 reviews

Golfing Bear

4.93 out of 5 average rating, 219 reviews

A private backyard features a heated pool surrounded by landscaped areas with palm trees and flowers. A covered porch provides shaded seating options, while lounge chairs invite relaxation by the water. A securely fenced area enhances safety and privacy.

Home in Navarre

Good times & tan lines! Only 5 miles to the beach!

A well-lit bedroom features a spacious bed dressed in neutral linens, complemented by warm-toned throw pillows. Two bedside tables with lamps flank the bed, and a piece of artwork depicting a coastal scene hangs above. Natural light filters through the window adorned with sheer curtains.

4.87 out of 5 average rating, 70 reviews

Modern Dream Home | Heated Pool and a Fire Pit!

Condo rentals with a pool

A serene waterfront view at sunset features a serene bay with multiple sailboats and yachts docked. The sky is painted in soft shades of pink and purple, reflecting on the calm water. A grassy area with kayaks and canoes is visible in the foreground.

4.92 out of 5 average rating, 133 reviews

Sunset on the Bayou near NAS/Downtown Pensacola

A bright living area offers views of the Gulf through expansive glass doors. The space features comfortable seating, including wicker chairs and a cozy sofa. A telescope stands nearby for observing the shoreline, while a balcony with seating is visible beyond.

4.99 out of 5 average rating, 139 reviews

Quiet Lux Family Beach Retreat

The outdoor pool area is surrounded by tropical palm trees and features a grotto waterfall. Natural stone formations enhance the scenery, with a thatched-roof cabana located nearby. The clear water reflects the blue sky, inviting relaxation and enjoyment.

4.95 out of 5 average rating, 237 reviews

Updated Coastal Chic Villa @ Purple Parrot Resort

4.79 out of 5 average rating, 214 reviews

A panoramic view of the Gulf of Mexico stretches across the horizon, showcasing clear blue waters meeting a sandy shoreline. Sunlight glistens on the water, creating a serene atmosphere. A few figures can be seen enjoying the beach, enhancing the tranquil coastal scene.

Condo in Navarre Beach

Welcome To Florida's Hidden Gem!

A bright waterfront scene is captured, featuring Little Sabine Bay with reflections shimmering on the water's surface. The view includes marinas with sailboats and yachts, framed by palm trees and gardens, with a pool visible in the foreground.

5 out of 5 average rating, 144 reviews

Stay at Sunshine Daydream on Pensacola Beach

4.88 out of 5 average rating, 146 reviews

The open living area features a dining table with four white chairs, a comfortable gray sofa, and a television mounted on the wall. Light enters through a window overlooking the sleeping area with a bed, enhancing the space’s relaxed atmosphere.

Condo in Navarre Beach

Footsteps away from beautiful beaches 🏖🏝⛱

4.96 out of 5 average rating, 265 reviews

A panoramic view of the Gulf of Mexico is captured from the balcony, showcasing a sandy beach leading to a long fishing pier. The water shimmers in shades of blue, with gentle waves meeting the shoreline under a clear blue sky.

Condo in Navarre Beach

10thFLOceanFrontFreeChairsUmbrellaHeatedPoolArcade

The living area features a comfortable sofa in light blue tones and a wooden coffee table. A ceiling fan is positioned overhead. A dining table with four chairs is set near a sliding glass door, which leads to a balcony offering views of the beach.

4.96 out of 5 average rating, 145 reviews

Perdido Skye 34 luxury beach vacation rental

Other holiday rentals with a pool

A serene view of the Gulf of Mexico showcases clear blue waters meeting a white sandy beach. The horizon extends across the image, with a few distant figures visible along the shore, highlighting the tranquil atmosphere of this beach setting.

4.99 out of 5 average rating, 88 reviews

Penthouse @ Sabine Yacht & Racquet Club

Superhost

An inviting backyard features a fire pit surrounded by four wooden chairs, illuminated by soft string lights overhead. A swimming pool is visible in the background, complemented by lush greenery and a clear sky at dusk.

4.8 out of 5 average rating, 81 reviews

Balinese Beach House w/ Pool, Huge Hot Tub & Sauna

4.97 out of 5 average rating, 63 reviews

A wooden deck is featured at the front of a small cabin, outlined by a sturdy railing. Comfortable seating is seen on the deck, shaded by a canopy. A circular firepit made of stone is located on the ground nearby, surrounded by gravel.

Guesthouse in Pensacola

The Rosales serenity suite

Guesthouse in Pensacola Beach

5 out of 5 average rating, 10 reviews

Gulf Breeze Bungalow

4.93 out of 5 average rating, 76 reviews

An outdoor patio is shown, featuring a fire pit surrounded by comfortable seating. A swimming pool is visible in the background, with lush greenery framing the area. The evening sky creates a serene ambiance, complemented by the flickering flames from the fire pit.

Guest suite in Pensacola

Private Suite with Saltwater pool

Guesthouse in Pensacola Beach

A private balcony features two turquoise lounge chairs positioned to offer unobstructed views of the bay. Lush greenery frames the scene, which includes a fishing pier extending into the water. A clear sky and distant land contribute to the peaceful atmosphere.

5 out of 5 average rating, 59 reviews

Pensacola Beach Waterfront Condo

A spacious tropical pool is surrounded by lush palm trees and a charming thatched-roof structure. The inviting water reflects the clear blue sky, while rock formations and gentle waterfalls enhance the natural beauty of the area. Lounge chairs are visible along the pool's edge.

4.95 out of 5 average rating, 81 reviews

Sea La Vie, Perdido Key, Florida

A spacious balcony features a glass-top table surrounded by four high-back chairs, offering panoramic views of the Santa Rosa Sound. The ceiling fan enhances comfort while the inviting blue sky and gentle waves create a serene coastal setting.